SYNTHESIS OF A METHYL HEPTAGLUCOSIDE WITH PHYTOALEXIN ELICITOR ACTIVITY-BASED ON OXIDATIVE COUPLING OF GLUCALS

Authors
TIMMERS CM VANDERMAREL GA VANBOOM JH
Citation
Cm. Timmers et al., SYNTHESIS OF A METHYL HEPTAGLUCOSIDE WITH PHYTOALEXIN ELICITOR ACTIVITY-BASED ON OXIDATIVE COUPLING OF GLUCALS, Chemistry, 1(3), 1995, pp. 161-164
Citations number
24
Categorie Soggetti
Chemistry
Journal title
Chemistry → ACNP
ISSN journal
09476539
Volume
1
Issue
3
Year of publication
1995
Pages
161 - 164
Database
ISI
SICI code
0947-6539(1995)1:3<161:SOAMHW>2.0.ZU;2-1
Abstract
Several suitable building blocks for the construction of the phytoalex in elicitor 3(2),3(4)-di-beta-D-glucopyranosylgentiopentaoside (2) wer e readily accessible by oxidative coupling of glucals. Block coupling of trimeric phenylseleno- and ethylthioglucosyl donors 17 and 18 with tetrasaccharide 16 in the presence of the thiophilic promoter N-iodosu ccinimide and catalytic trifluoromethanesulfonic acid furnished the de sired heptaglucan 2 in high overall yield.